Rachel A. Gupta, Esq., is a seasoned mediator and arbitrator who brings to her ADR practice many years of experience as a commercial litigator and former in-house counsel who handled complex commercial transactions, as well as securities, insurance, employment and other business litigations.

Ms. Gupta has over 20 years’ experience working with clients in the financial services, investment management and insurance industries. This includes nearly a decade in the role of in-house counsel, during which she handled multibillion-dollar “bet-the-company” and other high-profile litigation relating to the insurance of complex transactions, including residential mortgage-backed securities (RMBS), student loan asset-backed securities, credit default swaps, military housing projects and public finance bonds. She comes to the proverbial ADR table with firsthand experience as a one-time client who was responsible for negotiating billion-dollar settlements and dealing with companies’ internal operations, boards of directors, strategic decision-making, and formation of policies, procedures and corporate objectives—a knowledge base that provides her with an essential understanding of the variables at play for companies involved in ADR proceedings.

Ms. Gupta’s experience resolving complex business and commercial matters includes those involving alleged breach of contract, breach of fiduciary duty, fraud, negligence, unjust enrichment and other causes of action across industries, such as those in the financial services, securities, cryptocurrency, insurance, derivatives, hospitality, e-commerce, telecommunications, technology and real estate sectors.

Ms. Gupta’s experience transcends the world of high-stakes corporate disputes. Her ADR practice encompasses a wide variety of other practice areas involving small- and midsize-business disputes, including corporate governance matters and business dissolutions, as well as employment (e.g., discrimination, constructive discharge, executive compensation, noncompete agreements, sexual harassment, retaliation, and wage and hour), insurance, real estate and real property matters, among others.

The eclectic range of Ms. Gupta’s legal and business experience, combined with her strong interpersonal and communication skills, provides her with a fundamental understanding of the importance of what is at stake for parties—large and small, organizational and individual—on both sides of the negotiation table. All these qualities, in combination with her patience, creativity, persistence and dedication to hard work, uniquely position her to help parties engage in constructive dialogues when crafting practical solutions to their disputes.

Representative Matters

• Business Commercial
• Mediated pre-litigation dispute between government agency and technology company relating to installation of international fiber-optic network across 29 international sites
• Mediated alleged breach of contract and diversion of corporate opportunities claims relating to proposed project to digitally monetize gold mines and gold mine reserves
• Mediated claims for fraudulent conduct, including Racketeer Influenced and Corrupt Organizations (RICO) Act and fraudulent conveyance allegations, in connection with enforcement and collection of debt owed for business loan
• Mediated alleged breach of a letter of direction, as well as unjust enrichment and fraud claims, against bank in connection with loan funding Miami music festival
• Mediated breach of contract and fraudulent inducement claims in federal action involving software implementation contract
• Mediated pre-litigation dispute alleging breach of contract relating to services provided under litigation-expert consulting agreement
• Mediated litigation alleging claims of breaches of contract and fiduciary duty, and tortious interference related to software, licensing and exclusivity contract
• Co-mediated dispute between business partners of real estate management firm involving claims for alleged breaches of fiduciary duties and counterclaims for business dissolution
• Arbitrated dispute seeking damages arising out of point-of-sale (POS) services and products for restaurant and music venue
• Arbitrated and mediated multiple cases relating to alleged breaches of future receipts sales and/or royalty agreements
• Arbitrated dispute relating to student loan debt, alleging claims for relief under Federal Trade Commission’s (FTC) Holder Rule and for deceptive practices under New York General Business Law Section 349
• Employment Law
• Mediated federal litigation brought by former president and general manager of national cable provider, alleging claims for breach of executive compensation agreement, unjust enrichment, violation of New York Labor Law (NYLL) and counterclaims for breaches of fiduciary duty
• Mediated three pending class actions and nationwide collective cases alleging misclassification of certain employees as exempt under the Fair Labor Standards Act (FLSA)
• Mediated claim of religious discrimination and wrongful termination against art museum for allegedly failing to grant religious exemption to COVID-19 vaccine mandate
• Mediated dispute in which former legal assistant alleged age discrimination in connection with her termination from a boutique law firm
• Mediated federal litigation alleging disability discrimination claims brought by former employee against adult living community
• Mediated litigation alleging discrimination, hostile work environment and constructive discharge by physician assistant against a hospital
• Mediated numerous cases alleging violations of wage and hour laws (federal and New York state) brought on behalf of restaurant workers against former employers
• Co-mediated federal litigation involving claims of sexual harassment and retaliation brought by former employee against city agency
• Arbitrated, as member of tripartite arbitral panel, proceeding commenced by founding member of law firm involving allegations of breach of contract and fraud and seeking deferred compensation and alleged damages over $20 million
• Arbitrated claims filed against former employee for alleged breach of fiduciary duty and breach of contract
• Arbitrated matter involving alleged breach of restrictive covenants and confidentiality provisions of employment agreement
• Arbitrated matter involving allegations of racial discrimination, constructive discharge and retaliation by former employee against hotel employer
• Financial Markets
• Mediated litigation alleging breach of contract and securities fraud under Sections 10(b) and 20(e) of the Securities Exchange Act of 1934 filed by former employee against pharmaceutical company; involved alleged dilution of employee’s stock and fraudulent misrepresentations allegedly made in securities filings
• Mediated claims filed by financial institution alleging breaches of mortgage loan and conditional guarantees
• Mediated litigation in which plaintiff sought declaratory judgment seeking priority interest in deposit account against defendants, who contracted for future receivables of plaintiff-debtor
• Arbitrated dispute alleging breach of advisory services agreement for failure to issue warrants as compensation and involving question of whether agreement violated securities regulations
• Arbitrated dispute commenced by servicing agent of bank alleging breach of contract in connection with loan
• Represented, as private practitioner, multiple financial institutions, hedge funds and insurance companies in connection with claims of violations of securities laws, securities class actions and derivative actions, including matter against financial guaranty insurance company alleging that company and its directors and officers made material misstatements in connection with risk management and credit rating policies and procedures, credit mitigation strategies, internal financial reporting controls and loss exposures on its public finance bond portfolio
• Represented, as private practitioner, client in connection with multi-billion-dollar “bet-the-company” litigation involving alleged breaches of representations and warranties made in connection with the issuance and insurance of residential mortgaged-backed securities (RMBS)
• Advised, as private practitioner, financial institutions and hedge funds in connection with securities laws and regulations and corporate governance matters
• Insurance
• Mediated insurance coverage dispute relating to fire and collapse of wind turbine and tower
• Mediated federal litigation commenced by insurer seeking declaratory judgment relating to coverage under attorney professional liability policy
• Mediated federal litigation involving coverage for loss of high-speed boat under insurance policy
• Mediated federal litigation relating to denial of coverage under homeowners’ insurance policy for loss allegedly incurred in connection with water damage to vacation home
• Mediated litigation seeking to collect premiums allegedly owed under workers’ compensation policy
• Arbitrated, as chair of tripartite arbitral panel, proceeding in which insurer sought declaratory judgment that there was no insurance coverage under general commercial liability policy for insured and others in connection with claim for damages by injured worker on construction site
• Arbitrated, as panelist on tripartite arbitral panel, proceeding in which insurance broker asserted claims for fraud, breach of contract, tortious interference with business relations and retaliation against insurance company for commissions allegedly owed in connection with underwriting of insurance policies
• Represented, as private practitioner, clients in connection with litigations relating to interpretation of directors and officers (D&O) and employment practices liability insurance (EPLI) policies
• Real Property
• Mediated litigation alleging self-dealing and unauthorized conduct in management of 12 multifamily residential properties owned by family trusts through limited liability companies; involved claims for alleged breach of operating agreements, breach of fiduciary duties and request for declaratory judgment and injunction
• Mediated case alleging breach of commercial sublease filed by original tenant against subtenant, and related case filed by landlord against original tenant, involving defenses related to COVID-19-related business interruption and financial inability
• Mediated litigation alleging breach of contract in connection with sale of residential building in New York City
• Mediated case alleging breach of provisions of commercial construction contract relating to project for renovations at 16 buildings in New York City
• Mediated litigation involving allegations of breach of fiduciary duties by condominium association; action also included request for accounting
• Arbitrated dispute seeking specific performance in connection with loan sale because property securing one of the loans was allegedly encumbered by prior unreleased mortgage
• Smart Contracts & Blockchain
• Mediated alleged breach of contract, breach of warranty and fraud claims relating to purchase of data centers for cryptocurrency mining
• Arbitrated multiple cases relating to alleged unauthorized transfers of bitcoin, including, but not limited to, claims sounding in negligence, fraud and alleged violations of the Electronic Funds Transfer Act (EFTA)
• Advised, as private practitioner, client in connection with drafting and negotiations relating to cryptocurrency custody agreements

Honors, Memberships, and Professional Activities

Selected Awards and Honors

• JAMS Diversity Fellowship (member of the inaugural class of fellows), 2021–2022
• Associates Program, College of Commercial Arbitrators, 2023–2024

Selected Memberships and Professional Affiliations

• New York State Bar Association:
  • Co-Chair, Domestic Arbitration Committee, 2024
  • Member, Dispute Resolution Section, 2020–2024
  • Member, Commercial Federal Litigation Section (ComFed), 2022–2023, 2024
  • Member, Corporate Counsel Section, 2023
• New York City Bar Association, 2020–2023
  • Member, ADR Committee, 2020–2023
  • Co-Chair, Diversity Subcommittee, 2022–2023
• Member, American Bar Association, Dispute Resolution Section, 2022–2024
• Member, Steering Committee, Young Leaders in Alternative Dispute Resolution (Y-ADR), CPR, 2021–2024
• Secretary and Member of Board of Directors, ADR Inclusion Network, 2021–2023
• Member, New York Chapter, International Network of Boutique and Independent Law Firms, 2022–2023
• Member, ADR Panels:
  • Arbitration Panel, Financial Industry Regulatory Authority (FINRA), 2020–2024
  • American Arbitration Association (AAA), 2021–2024
    • Arbitration Panel, 2021–2024
    • Mediation Panel, 2022–2024
  • CPR Dispute Resolution, 2020–2024
    • Mediation Panel, 2020–2024
    • Arbitration Panel, 2021–2024
  • New York State Supreme Court
    • Commercial Division, New York County, 2020–2024
    • Bronx County, 2020–2024
    • Richmond County, 2022–2024
    • Kings County, 2021–2024
  • Mediation Panel, United States District Court, Southern District of New York, 2021–2024
  • Mediation Panel, United States District Court, Eastern District of New York, 2021–2024

Selected Presentations and Speaking Engagements

• Panelist, “Distinctive Ethical Landscapes: Exploring Arbitration vs. Mediation and the Diverse Roles Within,” Federal Bar Association, Jul. 10, 2024
• Trainer for Segment of “28-Hour Basic Mediation Training,” New York City Bar Association, Jul. 16, 2024
• Presenter, “Understanding the Mediation Process and Five Behaviors of Counsel That Can Lead to Impasse,” Riverside County Bar Association, Nov. 14, 2023
• Mock Arbitrator, “The Art of Impactful Opening and Closing Statements”; ICC Young Arbitration and ADR Forum (ICC YAAF), IBA Arb-40 and the Columbia International Arbitration Association (CIAA); Nov. 6, 2023
• Speaker, “The Changing Face of Mediation,” ALM General Counsel Conference, October 2023
• Panelist, “There Has to Be a Better Way: Changing How We Practice to Obtain Professional Satisfaction,” NYSBA ComFed and Dispute Resolution Sections (ComFed), Spring Meeting, May 6, 2023
• Moderator, “Co-Mediation: How to Ensure Two Heads Really Are Better Than One,” American Bar Association, March 8, 2023
• Panelist, “How to Start an ADR Practice,” Arbitration Committee, NYSBA Dispute Resolution Section, Jan. 10, 2023
• Moderator, “Early Mediation: Why, When and How,” CPR Global Conference, Dec. 7, 2022
• Moderator, “Handling Arbitrator Misbehavior” (perspectives from co-arbitrators, counsel and institutions), NYSBA Dispute Resolution Fall Conference, Oct. 20, 2022
• Moderator, “Arbitration Advocacy in the Virtual and Hybrid World, Session 3: When to Consider Mediation,” CPR Dispute Resolution, May 19, 2022
• Panelist, “Mass Arbitration Filings: How Are Arbitral Institutions Handling Them?” American Bar Association, March 17, 2022
• Panelist, “Hot Topics in ADR,” CPR Dispute Resolution Annual Conference, March 2022
• Presenter, “Bridging the Information Gap: Helping Clients Better Understand Mediation,” NYSBA DRS Mediation Committee, Feb. 8, 2021

Selected Publications and Media References

• “DEI & ADR: 5 Practical Ways to Increase Diversity in the Selection of Neutrals,” ACC Docket, June 2022
• “5 Mediation Mistakes That Create Obstacles to Settlement,” Law360, May 2022
• “Overcoming Client Misconceptions About Mediation,” ACC Docket, June 2021
• “Five Principles to Maximize Chances of Success in Mediation,” Mediate.com, Jan. 2021
• “Employment Litigation: 3 Instances Where Companies Should Consider Mediation,” Mediate.com, Sept. 2020

Background and Education

• Principal, Arbitrator, Mediator, Trainer; Gupta Dispute Resolutions LLC; 2020–2024
• Law Clerk, JAMS Inc., 2022–2024
• Senior Counsel and Chief Compliance Officer, Amaiya Management LP, 2019–2020
• Ambac Assurance Corporation, 2010–2019
  • Litigation Consultant, 2016–2019
  • First Vice President and Assistant General Counsel, 2010–2016
• Litigation Associate, DLA Piper LLP (US), 2006–2010
• Litigation Associate, Seward & Kissel LLP, 2004–2006
• Collateral Management Associate, Morgan Stanley Associates, 2001
• Municipal Syndicate Associate, Prudential Financial, 2000–2001
• Business Analyst, PricewaterhouseCoopers, 1999–2000 

Education

• J.D., cum laude, Fordham University School of Law, 2004
• B.A., magna cum laude and with Special Honors, The George Washington University, 1999

Bar Admissions 

• State of New York
• State of New Jersey
• United States District Court, Southern District of New York
• United States District Court, Eastern District of New York